225 homes sold in Wailea in the last year, at a typical $1.4M
Most homes sold are condos. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Wailea homes are listed.
Every place Wailea homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Wailea.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
62% of Wailea’s sales are condos, at $1.2M less than a house
64 houses and 120 condos sold in the year to May 2026. Condos sell faster.
typical sale · 64 sold in the year to May 2026
- Per square foot
- $1,023HI $625
- Days to sell
- 133
- Sold over asking
- 3%
- Listings with a price cut
- 18%
typical sale · 120 sold in the year to May 2026
- Per square foot
- $1,025HI $724
- Days to sell
- 123
- Sold over asking
- 5%
- Listings with a price cut
- 15%
Townhouses: 10 sold, typical $2.7M
Too few sales in 12 months for reliable figures.
Fewer homes sell than before 2022, at 1.8 times the 2016 price
225 sales in the last year, against 594 in 2021 and a low of 183 in 2025. The typical sale went from $774K in 2016 to $1.4M.
Source: Redfin Data Center, MLS sales; from June 2026 each month is a 3-month rolling window, its counts divided by 3. Typical price and $/sq ft are the monthly medians, weighted by sales. Redfin stopped publishing towns’ figures by property type after May 2026, so houses and condos are shown for the year to then.
What $1.4M buys in Wailea
Check a listing against what Wailea homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Wailea are back to pre-pandemic levels, with about as many homes for sale
We read every month of Wailea’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to September 2026, 225 sales.
If you’re buying in Wailea
- Shop in February. It brings about 42 new listings a month, close to the busiest month, with fewer bidding wars (10% over asking).
- Offer under asking. Buyers paid 94.4% of the list price on average; 4% paid over.
- You’ll usually have time. Only 16% of homes go under contract within two weeks; the typical one takes 125 days.
Fall brings the homes; spring brings the bidding wars
November has the most new listings (about 49 a month), but March is the most competitive: 15% of March sales close over asking. January and February offer nearly as much choice with fewer homes bid up (13%). February has the least competition (10%).
Averages for each calendar month, 2015 on.
Calmer than the 2021 frenzy, and calmer than Hawaii
| Wailea now | 2017–19 | 2021 peak | HI now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 4% | 6% | 21% | 16% |
| Gone within two weeksShare of homes under contract within 14 days | 16% | 20% | 40% | 24% |
| Price paid vs. askingAverage sale price ÷ list price | 94.4% | 96.5% | 98.9% | 97.4% |
| Days to sellMedian days from listing to contract | 125 | 132 | 92 | 97 |
212 homes for sale on a typical day
That’s twice the 2022 low (98), about the 2017–19 level and well under 2016’s 295.
Since 2019, houses are up 60%, condos 51%
A house typically sold for $2.3M in the year to May 2026 (64 sales), a condo for $1.1M (120).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Wailea ranks 41st of 43 busy Hawaii markets for bidding wars
Share of sales over asking in the last year, among towns with 60 or more sales. Wailea is one of the state’s calmer markets.
Source: Redfin Data Center, city figures, January 2012 to September 2026 (MLS sales, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Wailea home costs about $7,658 a month
Price: Wailea’s typical sale, last 12 months. Property tax at Wailea’s 0.2% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Wailea is affordable on local pay is on Cost of living.
Five things worth knowing
New listings in November
The month with the most choice. July has the fewest, about 31.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $1.4M home, about $3,050 a year.
Taxes vs. neighborsCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
Kihei, Kula, Pukalani, Kahului, Haliimaile and Wailuku sell for less a square foot
The busier markets within 25 miles of Wailea, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Kihei | 305 | $823K | $753 | 8% | 123 |
| Wailea | 225 | $1.4M | $937 | 4% | 125 |
| Wailuku | 174 | $847K | $652 | 12% | 104 |
| Kahului | 103 | $1.1M | $673 | 19% | 107 |
| Kula | 64 | $1.7M | $888 | 15% | 105 |
| Pukalani | 29 | $1.2M | $721 | 22% | 91 |
| Haliimaile | 24 | $1.5M | $810 | 4% | 973 |
Redfin Data Center, October 2025 to September 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Wailea, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Wailea. People who follow the town see it, and so do people comparing Wailea with their own town. No commission, no listing fee.
Questions about buying a home in Wailea
What do homes sell for in Wailea, HI?
225 homes sold in the year to September 2026 at a typical $1.4M, $937 a square foot. Houses sold for about $2.3M, condos for about $1.1M in the year to May 2026.
Is Wailea a buyer’s or seller’s market?
A buyer’s market: 184 homes were for sale in September 2026 and 19 sold, about 9.3 months of supply. Buyers paid 94.4% of asking on average.
When is the best time to buy in Wailea?
November brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Wailea?
About 0.2% of a home’s value a year. On a $1.4M home that’s near $3,050.
Where can I see homes for sale in Wailea?
Zillow, Redfin, Realtor.com and Homes.com all carry Wailea’s MLS listings; the search links above open each one filtered to Wailea.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted; from June 2026 each month is a 3-month rolling window, its counts divided by 3). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).